Highly Efficient Catalysis of Retro-Claisen Reactions: From a Quinone Derivative to Functionalized Imidazolium Salts

A new and efficient method for the preparation of several imidazolium salts containing an ester group in the C4 position of the aromatic ring through a retro-Claisen reaction pathway between a quinone derivative and several alcohols is described. This new organic transformation proceeds in the absence of a catalyst, but it is greatly catalyzed by different Lewis acids, especially with AgOAc at a very low catalyst loading and in very short reaction times. The process takes place by the nucleophilic attack of the carbonyl groups by the alcohol functionality, thus promoting a double C-C bond cleavage and C-H and C-O bond formation. This reaction represents the first example of this type between a quinone derivative and alcohols. A new and efficient method for the preparation of several imidazolium salts containing an ester group in the C4 position of the aromatic ring through a retro-Claisen reaction pathway is described. This new organic transformation takes place by the nucleophilic attack of an alcohol functionality over the carbonyl groups, thus promoting a double C-C bond activation (see scheme; Mes=mesityl).

• Autores: Visbal Acevedo, Renso Raul; Laguna, Antonio; Gimeno, María Concepción
• Tipo de recurso: Article of journal
• Fecha de publicación: 2016
• Institución: Corporación Universidad de la Costa
• Repositorio: REDICUC - Repositorio CUC
• Idioma: eng
• OAI Identifier: oai:repositorio.cuc.edu.co:11323/940
• Acceso en línea: http://hdl.handle.net/11323/940; https://repositorio.cuc.edu.co/
• Palabra clave: C-C activation; nitrogen heterocycles; retro-Claisen reaction; silver; synthetic methods
• Rights: openAccess
• License: Atribución – No comercial – Compartir igual